


Mistakes

by quaffanddoff



Category: 30 Rock
Genre: Anal Sex, Crack Treated Seriously, Disguise, F/M, First Time, First Time Bottoming, For once Kenneth isn't a total sub, Gender Confusion, Gender Identity Crisis, M/M, Oral Sex, Sexuality Crisis
Language: English
Status: Completed
Published: 2021-02-27
Updated: 2021-02-27
Packaged: 2021-03-15 08:21:57
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,134
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29681115
Author URL: https://archiveofourown.org/users/quaffanddoff/pseuds/quaffanddoff
Summary: Liz’s big mouth had gotten her into this mess. Now it would have to get her out of it.(Inspired by Season 6 Episode 11 "Standards and Practices," wherein Liz disguises herself as that elusive young rascal,Kenneth Toilethole.)
Relationships: Kenneth Parcell/Kenneth Toilethole, Liz Lemon/Kenneth Parcell
Kudos: 3





	Mistakes

**Author's Note:**

> Why are the weirdest, most obscure, most unpopular pairings the most fun to write?

No one could claim that Liz doesn’t look out for her friends.

When she’d heard Kenneth crying in the men’s room, it had broken her heart. The fact that she was partly to blame sent a wave of guilt sweeping over her, making her cringe with shame. Heedless of germs, she had reached out in a futile gesture, caressing the metal divider that separated their respective stalls as if she could pass through the wall and embrace her friend—or better yet, grab him and shake some sense into him. Even after all these years, after all that he had seen and been through, somehow he still remained that very same naïve farm boy who had first ventured up to the big city to pursue his lofty ambitions. None of the filth and obscenity he encountered could shake his faith or crumble the precarious pedestal on which he placed all his hopes and dreams. 

His innocence baffled her, but at the same time, it moved her. He had his share of issues, no doubt about that, but she couldn’t help but believe that if everybody tried to be a little more like Kenneth, the world would be a better place.

So in a misguided attempt to protect him, she had run her mouth and invented this preposterous lie. And now here she was, having to clean up her own mess. It was flat-out impossible to keep the promises she had made him, seeing as she could not arrange a dinner with a person who doesn’t exist, but she was still determined to do her best to make it up to him—to delay Kenneth’s inevitable disillusionment, to keep him as he was, pure and unsullied, just a little while longer.

Suggesting this dinner with the three of them had been one of the stupidest, most self-sabotaging ideas of her life; however, amazingly, through the combination of her willpower and Kenneth’s obliviousness, she actually managed to pull it off. She switched quickly back and forth between her regular clothes and her disguise again and again, making up a series of increasingly far-fetched and implausible excuses as the absurd evening wore on. 

It was Liz who said goodnight first. She gave some flimsy pretext and scurried out of the restaurant, leaving the two Kenneths alone to continue getting acquainted. Once she was gone, the conversation suddenly flowed much more smoothly. It was easier to talk without the disruption of Liz’s constant reappearances.

Liz was stunned by how much more comfortable she felt when pretending to be someone else. Maybe it was the clothes, which she’d swiped from Criss without asking (she had decided early on that it would be best not to run any part of this bizarre scheme past her new boyfriend, lest she scare him off so soon). The loose plaid shirt, denim jacket, slacks, and boxers were not substantially different from her normal clothes, yet the overall effect struck her as completely new and alien. Right away, she had found the unfamiliar sensation strangely satisfying. The extra-tight sports bra she’d worn flattened her chest for the occasion, and physically, it felt constricting, but mentally, not worrying about the shape of her figure for once was wonderfully liberating.

But maybe her newfound comfort wasn’t really related to her appearance at all. After all, she was feeling rather foolish in her bright red wig and moustache; she hadn’t even wanted to be a ginger but she had to accept her fate when there was only one matching wig/moustache combo at the costume shop. No, it wasn’t her clothes or accessories that made the difference. 

With her alter ego in the driver’s seat, something just _clicked_ between her and Kenneth. There was some indescribable new spark, which Liz knew must be connected to the shift in gender dynamics between her and her employee. Relating to him as a man for the first time was just…different, somehow. She couldn’t account for why, exactly, but she knew it was better.

By the end of the meal, neither Kenneth wanted to say goodnight. Before she could stop and think better of it, Liz impulsively offered to drive Kenneth home; only then did she remember that she didn’t actually own a car (she had excused herself to “feed the meter” so many times that night that she eventually started to believe her own alibi). She turned in an Oscar-worthy performance feigning outrage that it had gotten stolen right off the street, then offered to accompany him home on foot instead.

As they boarded the subway together, she silently berated herself for her lapse in judgment. What was it about this invented persona that seemed to give her a pathological inability to make rational choices? They rode the train sitting side-by-side but with a good amount of space between their seats, not speaking much because that’s not what men do. Men sit far apart and talk in low, gruff voices, exchanging only those words which are absolutely necessary to communicate and nothing more.

It was getting late but the train was still crowded with Friday night revelers, and the two Kenneths were gradually pushed closer together by throngs of rowdy passengers. Eventually they were close enough that their knees brushed with every lurch of the train. Each jolt was accompanied by a corresponding jolt in Liz’s stomach. Neither Kenneth acknowledged the contact. They only offered each other small, subtle smiles. 

And when they reached Kenneth’s apartment, Liz wasn’t yet ready for this new easy comfort that had grown between them to end. So she accepted his invitation to come upstairs, then she accepted his invitation to have another drink. 

If this were anyone else, she would know exactly what was about to happen at this point in the proceedings. But it wasn’t just anyone, it was _Kenneth_ , and therefore, what she thought was about to happen couldn’t possibly be happening. She wasn’t entirely sure what his deal was—whether it was a religious thing, a Southern thing, or just a weird personal quirk of his, whether he was repressed, asexual, or prude—but she assumed sex was out of the question.

But after a few drinks, she accepted a whole other kind of invitation, one that he seemed just as surprised to offer as she was to receive.

All night long she had been cursing herself for making irresponsible choices and reckless decisions, for writing checks she knew her ass couldn’t cash. Since this whole ridiculous saga had begun, she had been making mistake after mistake, cobbling together needlessly complicated solutions to try and fix her problems but, in the process, only compounding them. But despite all the stress and hassle, as Kenneth led her to his bedroom, gathered her in his arms, and leaned in to kiss her, she couldn’t bring herself to regret a single one of the idiotic mistakes that had led her here.

That evening Liz had three surprising new realizations:  
Kenneth was into guys.  
_She_ was into _being_ a guy.  
As a guy, she was into Kenneth.

How far was Liz willing to go to help a friend? She had asked herself that question many times, but never before had she been more eager (or more afraid) to find out the answer. She knew her dedication was about to be put to the test. In the past, there were certain lines she would never have considered crossing, but tonight, those boundaries suddenly didn’t seem so rigid. She was pretty confident she could convince herself to go through with this. In fact, she was surprised to discover that she _wanted_ to do it.

From the very start of this crazy night, she had known that pulling off her trick would involve a lot of strategic maneuvers and careful finessing. Once she found herself in Kenneth’s bed, she realized she was going to have to access an entirely new realm of stealthy deception.

Liz’s big mouth had gotten her into this mess. Now it would have to get her out of it.

Normally, she wasn’t the biggest fan of this particular activity, but tonight, as she knelt down before Kenneth, situated herself between his feet, and licked her lips, she felt a renewed appreciation for the act. She felt clever for thinking of a way to pull this off that wouldn’t give away her secret. Plus, the way he groaned and seized her head to control her motion, guiding her up and down in his lap, was actually pretty hot. But then he tugged her back up to her feet and she felt his hand stray towards her crotch. She panicked and moved his hand to her ass instead to divert his attention. To her great surprise, sweet, innocent, naïve Kenneth immediately took the suggestion and ran with it.

It would seem as though she had misjudged him.

He pushed her down onto the bed, flipped her over on her stomach, and tugged at her pants. She gulped nervously and allowed him to pull them off, giving a quick prayer of thanks that they’d left the lights off and the room was dark. She flattened herself to the bed, positioning herself in such a way as to keep the front portion of her body strictly out of play, leaving him no choice but to tackle the rear. He began exploring her with gentle, probing fingers, which started as a light mischievous tease, then soon turned into something more serious. 

Facedown on the mattress, Liz’s teeth were gritted and her hands were clamped onto the sheets with an iron grip. She knew this would all go much better if she relaxed, so she took a deep, calming breath and tried to unclench. Kenneth had never touched her like this before, and _no one_ had ever touched her _there_ before, so she was doing her best to assimilate several new experiences at once. She had always been curious what exploring this arena would be like but never felt empowered to give it a try. As it turned out, it felt wrong and bad and strange and incredible all at the same time. He worked her open slowly until she was ready, prepared to do what guys like her do. He withdrew his fingers and replaced them with something thicker, harder, and better.

Her disguise had held up well during dinner but this newest development tested it on a whole other level. She wasn’t too concerned about the wig, which was fastened securely with an assortment of clips and pins—it was the moustache that was causing the real trouble. The spirit gum had performed admirably during dinner but now, with her face mashed into a pillow, its adhesion was being threatened. She felt it slip as her face contorted in a mixture of pleasure and pain. One particularly enthusiastic thrust dislodged the moustache completely and she scrambled to stick it back on before Kenneth noticed anything was amiss.

The other challenge was her voice. It was a struggle to continually remind herself to throw in a “dude” or a “bro” in every sentence to keep things sufficiently manly, and artificially lowering her pitch was making her throat sore. All that was hard enough to manage, but taking things to the bedroom had promoted her task from tricky to downright impossible. She tried her best to make her involuntary gasps and moans sound deep and masculine, but she found she didn’t have much control of the sensual noises being coaxed from her. So she let herself squeal and shriek and simply justified it as a character choice.

In her too-high voice she cried out a name, the one name, the only name, and didn’t know whether she was saying his name, or _his_ name, or her own.

The next time they meet up, Liz doesn’t come along to chaperone them. Everything that happens from then on is private, just between two bros. It becomes a recurring thing, an honest-to-God affair. They experiment. They switch roles (thanks to Liz’s nifty new toy). They wake up next to each other in the morning and do it all again. The two Kenneths don’t acknowledge what they are, what they’re doing, or what they mean to each other, because they’re both guys and guys don’t talk like that. They just let it happen.

Until one day, when the other Kenneth shows up on the first Kenneth’s doorstep with no baggy shirt or pants, no wig, and no moustache. He holds his breath as Kenneth takes in the sight of his long brown hair, his smooth skin, his curvy figure. They lock eyes for a while as they both silently reevaluate everything they thought they knew. Eventually, finally, Kenneth smiles and stands back, letting the other Kenneth pass through the threshold, welcoming him inside.


End file.
